1. Why Kennebunkport Is the Perfect Base for Day Trips
Kennebunkport isn’t just one of those “cute little New England towns” you see on postcards—it’s actually a fantastic jumping-off point for exploring the rest of southern Maine (and even a bit of New Hampshire if you’re feeling adventurous). It’s small, yes, but it’s got this cozy harbor vibe, fresh seafood spots that smell like heaven, and the kind of streets that make you want to wander without looking at your phone for directions.
And here’s the thing—you can wake up in Kennebunkport, have a slow breakfast (lobster omelet, anyone?), then hit the road and still be somewhere totally different in under an hour. Want beaches? Easy. Want a lighthouse tour? Done. Want to eat your way through a string of Maine coastal towns? Buckle up.
Another reason this spot works so well for day tripping is the balance—it’s touristy enough that you’ve got plenty of places to stay and eat, but small enough that you can escape the crowds in just a few turns. I’ve done trips from here in every season, and the variety still surprises me. In summer, you’re chasing sea breezes; in fall, it’s all about foliage and apple cider. Even in winter, you can do snowy coastal walks that feel straight out of a movie.
If you’re planning your own Kennebunkport travel, think of it like your home base—a comfy, lobster-roll-filled headquarters for coastal adventures. Just remember: the roads can be winding and slow, so you’ll want to leave earlier than you think. But trust me, the payoff? Totally worth the gas.
2. Ogunquit – Beaches, Cliff Walks, and Artsy Vibes
Drive time from Kennebunkport: about 30 minutes.
Ogunquit feels like it was designed for people who can’t decide if they want a beach day or a culture fix—because you can do both here without breaking a sweat. First stop, obviously, is Ogunquit Beach. It’s huge, clean, and the kind of sand you can actually walk barefoot on without hopping around like the ground is lava. If you’re here in summer, bring snacks and an umbrella, because once you stake your spot, you won’t want to leave.
But if you’re like me and can’t just sit still all day, the Marginal Way is where you’ll fall in love. It’s a cliffside path about a mile long, with views that make you stop every five minutes to say, “Okay, THIS is the best one.” (Spoiler: they keep getting better.) The walk ends in Perkins Cove, which is basically a little fishing village turned boutique-and-restaurant hotspot. If you want the freshest lobster roll of your life, grab one here.
Ogunquit also has this unexpected artsy streak thanks to the Ogunquit Playhouse and a handful of galleries. It’s a place where you can go from eating fried clams on a pier to sitting in a theater watching a Broadway-quality show, all in the same afternoon.
One tip? Parking can be a pain in peak season. If you see an open spot, take it and walk—it’s part of the charm, and you’ll probably discover a café or two along the way.
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3. Portland – Foodie Heaven on the Water
Drive time from Kennebunkport: about 40 minutes.
If Kennebunkport is laid-back coastal charm, Portland is like its hip, slightly louder cousin who knows all the best places to eat. This city’s Old Port district is full of cobblestone streets, salty air, and restaurants that take “local seafood” very seriously. You can’t go wrong with Eventide Oyster Co. for oysters and brown butter lobster rolls (yes, brown butter—it changes your life).
The great thing about Portland is that you can easily make it a food-focused day trip or mix in some sightseeing. The working waterfront has fishing boats unloading their catch right next to trendy breweries. There’s the Portland Head Light in Cape Elizabeth—probably the most photographed lighthouse in Maine—which is a short drive from downtown and worth the stop.
Shopping here is also solid if you like indie boutiques, local art, and stores selling things you didn’t know you needed until you saw them. And if you’re into history, the Wadsworth-Longfellow House and the Victoria Mansion are both fascinating in that “I didn’t think I cared about old houses but now I do” kind of way.
Pro tip: come hungry and pace yourself. Portland has so many good food spots that you’ll either wish for a bigger stomach or regret that third lobster roll (been there).
4. Portsmouth, New Hampshire – A Quick Hop Across the State Line
Drive time from Kennebunkport: about 50 minutes.
Yes, I know—it’s not even in Maine. But hear me out: Portsmouth is one of the most walkable, interesting little cities in New England, and it’s close enough that you can be there before your morning coffee wears off. The historic downtown is loaded with brick buildings, boutique shops, and restaurants that feel like they’ve been here forever.
If you like history, Strawbery Banke Museum is a must—it’s this outdoor living history museum where you can wander through centuries-old houses and watch craftspeople do their thing. But even if you skip the museums, Portsmouth is just a great place to stroll. Every few steps, you’ll find a café, an antique store, or a bookshop you want to duck into.
The waterfront here is more river than ocean, but it’s still beautiful, especially if you grab a table at one of the restaurants with outdoor seating. And if you’re into breweries, Portsmouth Brewery and Earth Eagle Brewings are worth checking out.
One warning: parking can get tight on weekends, so either come early or be ready to circle the block a few times.
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5. Wells and the Rachel Carson National Wildlife Refuge
Drive time from Kennebunkport: about 15 minutes.
Wells is often overlooked because it’s so close to Kennebunkport, but that’s actually what makes it perfect for a low-effort, high-reward day trip. The beaches here are wide, flat, and a little less crowded than some of the bigger-name spots—perfect if you just want to throw down a towel and read a book with the sound of waves in the background.
But the real gem here is the Rachel Carson National Wildlife Refuge. Even if you’re not a “nature person,” the trails are short, easy, and ridiculously peaceful. You’ll see salt marshes, birds, and views that look like they belong in a painting. The air here smells different—cleaner somehow—and it’s the kind of place that forces you to slow down.
If you’re hungry afterward, Wells has some great seafood shacks where you can eat with your hands and not feel bad about it. Think fried clams, lobster rolls, and chowder that tastes like someone’s grandmother made it from scratch.
Wells might not have the flashiest attractions, but sometimes that’s exactly the point—it’s a reset button in the middle of a busy trip.
6. Cape Elizabeth – Lighthouses and Cliffside Views
Drive time from Kennebunkport: about 50 minutes.
Cape Elizabeth is one of those places where you can go from “Wow, that’s pretty” to “Okay, I need to move here” in about five minutes. The big draw is Portland Head Light, and yeah, it’s every bit as photogenic as you’ve heard. It sits right in Fort Williams Park, so you can wander the trails, check out the old fort ruins, and picnic while waves slam into the rocks below. There’s something oddly hypnotic about just watching that light spin while the wind whips around you.
And it’s not just about the lighthouse—Cape Elizabeth has some of the most rugged, beautiful shoreline in southern Maine. If you’re into photography, you’ll fill your camera roll before lunch. If you’re more of a “just enjoy the view” person, grab a coffee from one of the local spots and park yourself on a bench overlooking the Atlantic.
One of my favorite parts? The food trucks. In summer, you’ll often find Bite Into Maine parked here, serving lobster rolls that somehow taste even better with ocean spray in the air.
The vibe is calm, almost meditative. It’s not a “do everything” kind of stop—it’s a “slow down and notice the details” spot. And honestly, after a few busier day trips, that’s exactly what you need.
7. York – Beaches, a Cliff Walk, and a Giant Taffy Store
Drive time from Kennebunkport: about 45 minutes.
York might not get the same hype as Ogunquit or Portland, but it’s got this low-key charm that sneaks up on you. First off, there’s Long Sands Beach, which is exactly what it sounds like—long, sandy, and perfect for a walk or an afternoon of just… doing nothing. If you prefer smaller crowds, Short Sands Beach is right near the downtown area and has more of that classic “boardwalk” feel.
York’s Cliff Walk is another underrated gem. It’s not as long as the one in Ogunquit, but the views are still gorgeous, and you’ll probably have more space to yourself. Plus, York is home to Nubble Light, one of the most photographed lighthouses in New England. It’s perched on its own little island, and you can get those classic “waves crashing” shots without much effort.
And then there’s The Goldenrod. This place has been making saltwater taffy for over a century, and you can actually watch them pull and cut it right in the window. Even if you’re not into taffy (I’m more of a fudge person), it’s worth a stop just for the experience.
York is one of those places that feels like summer even if you visit in October. It’s got that easy, nostalgic energy that makes you want to linger a little longer than you planned.
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8. Biddeford – A Mill Town Turned Cool
Drive time from Kennebunkport: about 20 minutes.
Biddeford used to be the kind of place people just drove through on their way to somewhere else. Now? It’s having a full-blown moment. The old mill buildings have been turned into breweries, coffee shops, and restaurants, and the downtown feels like it’s buzzing with this creative energy.
If you’re a coffee snob, Elements is a must—it’s part café, part bookstore, part beer bar, and somehow it works. For food, check out Palace Diner, which looks like a vintage train car and serves some of the best breakfast sandwiches you’ll ever eat.
But Biddeford isn’t just about food. The revitalized riverfront is great for a stroll, and nearby Biddeford Pool offers quieter beaches and salt marshes if you want a more nature-focused detour.
What I like about Biddeford is that it still feels authentic—there’s no “trying too hard” vibe. It’s just a real Maine town that happens to have great coffee, good food, and a growing arts scene.
9. Kennebunk – Right Next Door, but Totally Different
Drive time from Kennebunkport: about 5 minutes.
Yes, it’s basically around the corner, but Kennebunk is worth its own day trip. The downtown here is a little more “classic Main Street” compared to Kennebunkport’s harbor focus. You’ll find antique stores, local galleries, and some excellent bakeries (Boulangerie makes bread so good you’ll want to buy extra just to freeze).
If you’re into history, the Brick Store Museum is surprisingly engaging—it covers everything from shipbuilding to local art. And the Mousam River runs right through town, giving it a peaceful, small-town feel even when there’s a bit of traffic.
Kennebunk Beach is a short drive from the center, and it’s a great place for a walk no matter the season. In summer, it’s lively with families and sunbathers; in winter, it’s all about bundled-up locals walking their dogs with the wind in their faces.
It’s an easy, no-pressure kind of trip—perfect if you just want to explore without racking up too many miles on the odometer.
10. Scarborough – Beaches and Birdwatching
Drive time from Kennebunkport: about 35 minutes.
Scarborough doesn’t get the same buzz as some of the bigger Maine coastal towns, but it’s a fantastic choice if you’re into quieter beaches and nature. Scarborough Beach State Park has some of the warmest water in Maine (relatively speaking—it’s still Maine), and the sand stretches out forever.
Nearby, you’ve got the Scarborough Marsh Audubon Center, which is the largest salt marsh in the state. You can rent a kayak or canoe and paddle through the channels, spotting birds and feeling like you’re way farther from civilization than you actually are.
And if you’re up for it, Higgins Beach is a local favorite—smaller, relaxed, and with some great surfing when the conditions are right.
Scarborough is one of those places where you can mix active stuff with pure relaxation. Paddle in the morning, nap on the beach in the afternoon, and grab dinner in Portland on your way back to Kennebunkport.
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11. Freeport – Shopping and Shoreline Trails
Drive time from Kennebunkport: about 1 hour.
Freeport is famous for one thing above all else—LL Bean. The flagship store is open 24/7 (yes, really), so if you’ve ever had the sudden urge to buy a kayak at 2 a.m., this is your spot. But it’s more than just a shopping trip. The downtown is lined with outlet stores, small boutiques, and cafés that make it dangerously easy to lose track of time.
If you need a break from the retail madness, Wolfe’s Neck Woods State Park is just a few minutes away and offers peaceful trails along Casco Bay. You’ll find osprey nests, rocky shorelines, and plenty of picnic spots where you can escape the crowds. It’s the perfect way to balance out a morning of swiping your credit card.
Food-wise, Harraseeket Lunch & Lobster is a casual, no-frills dockside spot where the seafood is as fresh as it gets. Picture eating a lobster roll while watching fishing boats unload their catch—that’s Freeport.
It’s an easy, satisfying day trip because you can tailor it to your mood—shop till you drop, hike until your legs protest, or mix both for the best of both worlds.
12. Old Orchard Beach – Boardwalk Fun and a Retro Pier
Drive time from Kennebunkport: about 35 minutes.
If you’re craving that classic summer beach-town energy, Old Orchard Beach delivers. The main stretch of sand here is wide and busy, with a pier that juts out into the water like it’s straight out of a vintage postcard. The pier is packed with restaurants, bars, and shops, and in summer, the air smells like fried dough and salty popcorn.
There’s also Palace Playland, an old-school amusement park right on the beach. You can ride a Ferris wheel with ocean views or go full nostalgia with bumper cars and arcade games. It’s one of the few spots in Maine where you can get a dose of carnival fun alongside your beach time.
Old Orchard Beach isn’t subtle—it’s bright, loud, and unapologetically touristy—but sometimes that’s exactly what you’re in the mood for. You can spend the morning swimming, the afternoon playing mini-golf, and the evening watching the sunset from the pier with an ice cream cone in hand.
Pro tip: this place gets packed on hot summer weekends, so either come early or embrace the chaos.
13. Bath – History, Boats, and a Laid-Back Waterfront
Drive time from Kennebunkport: about 1 hour 15 minutes.
Bath calls itself “The City of Ships,” and once you see the massive shipyard on the river, you’ll get why. This is a working waterfront, not just a tourist attraction. The Maine Maritime Museum is the big draw, with exhibits on shipbuilding, fishing, and life on the coast. It’s the kind of place where you’ll leave knowing way more about boats than you planned (in a good way).
The downtown is small but full of character—brick buildings, local shops, and a few solid spots for lunch. If the weather’s nice, Waterfront Park is a great place to just sit and watch the river traffic.
Bath doesn’t try to be flashy, and that’s part of the appeal. It’s slower, quieter, and feels more authentic than some of the bigger tourist towns. Plus, the drive there takes you through some beautiful stretches of midcoast Maine, so half the fun is getting there.
14. Popham Beach State Park – Endless Sand and Stunning Views
Drive time from Kennebunkport: about 1 hour 30 minutes.
Popham Beach is one of the most impressive beaches in Maine—long, wide, and backed by dunes that make it feel wild and untouched. At low tide, you can actually walk out to Fox Island, which sits just offshore (just make sure you keep an eye on the tide, because getting stranded would be… awkward).
The water here is chilly even in summer, but that doesn’t stop people from wading in. It’s also a popular spot for picnics, kite flying, and just wandering along the shoreline collecting shells.
If you’ve got time, nearby Fort Popham is worth a look. It’s an old Civil War-era fort made of massive granite blocks, and you can walk through it for free. There’s something surreal about exploring those empty stone rooms with the ocean right outside.
Popham isn’t overly built up, so you’ll want to bring snacks or plan to eat in Bath on your way back. But that’s part of what makes it feel like a true escape.
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15. Boothbay Harbor – Classic Maine on the Water
Drive time from Kennebunkport: about 2 hours.
Okay, this one’s a bit of a stretch for a “day” trip, but if you start early, it’s worth it. Boothbay Harbor is the kind of place you picture when someone says “quintessential Maine coastal town.” It’s got working fishing boats, sailboats bobbing in the harbor, and streets lined with seafood shacks, ice cream stands, and souvenir shops.
One of the highlights here is taking a boat tour—whale watching, puffin cruises, or just a scenic sail around the islands. On land, the Coastal Maine Botanical Gardens are stunning, especially in summer when everything’s in bloom.
Even just wandering downtown is a treat—you’ll find little art galleries, fudge shops, and waterfront benches where you can just sit and watch the harbor activity.
It’s a longer drive, but Boothbay feels like a reward at the end. By the time you head back to Kennebunkport, you’ll have that happy, tired feeling that only comes from a day well spent by the water.
Wrapping Up Your Kennebunkport Day Trip Plans
By now, you’ve probably realized something: you could stay in Kennebunkport for a full week (or two) and still not run out of easy day trips. That’s what makes this part of Maine so good for travelers who like variety. You can wake up one morning and decide you’re in the mood for a quiet beach walk, then spend the next day hopping from shop to shop in a bustling port city.
Another bonus? Most of these trips are under an hour away, which means you don’t have to spend half your vacation in the car. Even the “longer” trips like Boothbay Harbor or Popham Beach feel doable if you start early—and the drives themselves are part of the fun. Coastal Maine roads weave through pine forests, marshlands, and tiny towns that look like they’ve been frozen in time.
If you’re coming for the first time, my best advice is this: don’t overplan. Sure, pick a few must-sees, but leave some space for detours. Maybe you spot a roadside lobster shack with a line out the door—that’s your lunch now. Or you drive past a tiny beach you’ve never heard of—pull over and check it out. Some of the best memories happen when you’re not following a schedule.
And when you come back to Kennebunkport after each trip, you get to end the day the way Mainers do best: with a good meal, a view of the water, and that salty air that sticks in your hair.
FAQs About Day Trips from Kennebunkport
Q1: What’s the best time of year for these trips?
Summer gives you the warmest weather, open attractions, and full beach days. Fall is gorgeous for foliage and fewer crowds. Spring can be quieter, but some seasonal spots might still be closed. Winter has its own charm—think fewer tourists and snowy coastal walks.
Q2: Do I need a car for these day trips?
Yes. Maine’s coastal towns aren’t super connected by public transit, and the beauty of these trips is the flexibility to stop wherever you want.
Q3: Which trip is best if I only have half a day?
Wells, Kennebunk, and Biddeford are super close and easy to explore without rushing.
Q4: Are these trips family-friendly?
Absolutely. Most destinations have beaches, parks, and easy walking areas. Just check ahead for specific activities if you’re bringing younger kids.
Q5: What’s the best “hidden gem” spot near Kennebunkport?
Rachel Carson National Wildlife Refuge. It’s quiet, scenic, and so close that you can squeeze it in even if you’ve only got a couple of free hours.
